I remember having a terrible time with Madden NFL game ports in the early 2000s. One of them was so incredibly bad that it became a running joke for my brother and I, and I will never remember the old EA slogan the same way again. I think it was 2002, 2003 or 2004... it would crash before even finishing the EA logo video.
Our entire experience with the game consisted of:
"E....A.... Sports.... It's in the game-ame-ame-ame-ame-ame-ame..." and after doing that for a while the system would eventually blue screen or reboot. The PC ran everything else perfectly fine, so it was just this game... ame ame ame. *ahem* Sorry.
I don't know how many times we tried to make it work before giving up and probably returning it (which was very difficult with open boxed software).